Production of acetyl-cleve&#39;s acid



be understood that it is not limite are charged into a jac I 25 rity) tation lShCOiltl vhar 3 Thecharge in the Cleves acid, and is sub ic acids and from water. sis thus carried out, the small amount Patented Get. 21, 193G nnirsns ar WALTER M. RALPH, on BUFFA O; NEW vonxjassisuon' {no N. Y, AQ'CORBORAQIQIWQN on NEW YORK CHEMICAL oo.,- INo.,- on new YORK,

'NATIONAL Autumn j zeno'ntrcrronon ACETYL-CLEV ESACIDiii Iio Drawing. Orig'inal application filed .Tulyfl,

According to'the present inven acid, that is, l-naphthylamine-6;monosul ionic acid and 1-n aphthylamine-7-monosulfonic acid, either-separately or in admixture, I

is heated in the form of the free acid with glacial acetic acid and sodiumacetate where by the monoacetyl derivative, that is, acetyl- I particularly.

Oleves acid, is produced. The invention willbe by the following specific example,

further illustrated but it will The parts'are by weight. a p

Example: 530 parts of glacial acetic acid keted silicon iron (duvriron) kettle provided with, an agitator and reflux condenser. 136 parts of crystallized 1 sodium acetate or 82 parts stantially anhydrous so added, and finally-223 parts (one H101)" of dry Gleves acid (based on 100 per cent 'pu- The kettle is theniclosed, and the con tents brought to aboil and allowed to with agitation, end of this time, the water present are nued throughout the tion and the distillation isc'arriedto' such a point thata sample'removed fromthe kettle dens within about five minutes tosuch an the excess of acetic acid and distilled'off." The agiextent that it may be bottom discharge'opening,

example througha I where it is-permitinto a suitable receptacle, ted to cool and harden.

comprised chiefly ofthe sodium salt of acetyl-.

stantially free from the salts ofinorgan 7 When theproces product will contain only a very "of unacetylated material, for example, one

or two percent or product being substantially free from, salts of inorganic acids andpracticallyfreefrom water is particularly suitable, toruse in many such as subsequent p-tate. r Q o a 'lfhe method at produ in ac ty1- reactions, for example,

application'filed November 29,

d thereto.

(one mol) of subdiurn acetate are then distill'abroken by .a sharp blow:

kettle'is then removed, for 5 The dry product; is

less. Further, the solidi 1925. Serial n laasss. te fby i ticniiff he".t ddu bngbir n tro acetyl-Cleves'j acid as described; in the pare 1920, se i at; 427,115.; a s and this t application "of whichjthi's application 1 is a-divisi1on.;.' It may be'pointed out-that be sides the alkali meta1 acetates,e. g.,;so'dium acetate,- acetate 'for; example, the alkaline. earth metal acetates, such as calcium acetate, etc;

T The uses important advantage, as, compared with the use of the dry sodium salts of Clevels acid,

, from themanufacturing viewpoint, mammary freeflacid easily obtain-J able*w v i paring the'dry so can nevertheless the; manner above acid is not attacke by glacialacetic aci acetate is also present, the free. acid is gap parently converted; progressively: into. the

form of it i i dium salts' ,b'ut-th e free acid ithoutthefdifficultiesinvolvedin prerg' 7.

be effectively, acetylated in described, The free Cleyefs d, or"'is attacked b'ut little, 1 v

(1 alone, but whensodiurn V 65 s of other metalsmey be used,

fthedryitree Cleyes acid has I s sodium salt which then reacts fv with the glacial acetic acid to give the'acetyl' 7 compound. The reac sodium acetate appears to bean equilibrium reaction, such that only a small amount of the sodium salt is formed and present at any tion of the free acid with one time, but the reaction of this salt with the acetic acid destroys the equilibrium and the reaction therefore proceeds to substantial completion in a gradual and progressive manner. 1

, This metho ,is applicable to the 'acetvlationof other aromatic amidoesulfonic acids.

' This application i a cation filed Novemb 427.116, which has in 1,566.425;

i I claim:

'1, The'meth Cleves acid which comprises inducing a reer 29, 1920, Serial No;

action between Clev'e7s "acid and glacial acetic d of producing monoacetyld ofacetvlation of Cleves acid atured into Patent No, a

action between Cleve s acid and glacial acetic acidiin the'presence of analkali' metal ace 1 f e0 0d of producing monoacetyl Cleves acid which comprises inducing a re- 7 actlon between Cleves acld and glaclal acet1o acid 1n the presence of sodium acetate.

4:. The .method of producing monoacetyl- Gleves acid which comprises heating a mixtureof Clevs acid, glacial; acetic acid and sodium acetate tothe boiling temperature.

5. The method of producing monoacetyh ture f- Q jev acid} sodium acetate to the brittle solid. 6. The method of tune of CIeVesacid, glacialacetic acid and sodium acetatetoza refluxing temperature for about 24 "hours and then subjecting the mass tofdistill'ation until 'a-residue is obtained which 'hardens upon cooling toa solid, 1

7 In the productionfof mon'oacetyl-Cleves' a o ime hqd w i j h mol of" amasse acetate in thepresence of an excess of glacial eetifie fdl 8. Litheproduction of monoacetyl-Cleves acid, the process which comprises heating one molof Clev'es acid inthe. free statewith at, 5 least one mol of sodium acetate in'thepres'e ence of more than one mol of" glacialacetic acidiat refluxing-"temperature; and distilling and 'wate r from the reaction ofi acetic acid re- Y n a In'testi'm-ony whereof I affix'my signature."

Q L ERM R L -i.

I produoing nonoacetyl o' Cleves ac d whichf com'pr 'sesf'heatlngr 21; m'lxcomprisesrheating one 3 a with one mo-l of SOCllIlIIL 

